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$1,675,000
3 Beds ⋅ 3 Baths ⋅ 619893 MLS
Enjoy gentle breezes and exceptional water views from this new home! Luxury Waterfront in the Upper Keys Stunning waterfront residence with peaceful water views, gracefully positioned on an expansive stately setting. Designed with understated elegance and modern coastal sophistication, this exceptional 2-story home features vaulted ceilings, an open light filled layout and generous living spaces that feel comfortable and inviting. The beautiful designer kitchen showcases top of the line appliances, quartz waterfall island with gorgeous cabinetry. This is refined living with all the comforts expected in a luxury home. A thoughtfully designed split-bedroom floor plan offers 3 bedrooms and 2.5 baths, creating both comfort and privacy. Ideal to entertain with a separate dining, refreshment area, and office space. Turn an everyday shower into a spa experience. Walk-in showers, bench seating, water closets and ample storage. The large waterfront terrace provides the perfect setting to relax and enjoy the tropical breezes and tranquil views. Covered parking, abundant storage, and ample room for a future pool and outdoor entertaining. Create your own oasis on this remarkable property. Located just across from bayfront homes, this residence captures the essence of luxurious Florida Keys living with peaceful breezes, open views, and timeless coastal charm. Enough room to store your water toys and become a member of private club to use boat ramp nearby.

38 N Bounty Ln, Key Largo
$3,400,000
5 Beds ⋅ 5 Baths ⋅ 619897 MLS
CONSTRUCTION COMPLETE! SeaGlass Cove is a brand-new luxury, gated island community located in the heart of the Florida Keys, adjacent to Duck Key. A rare find of just 14 new construction residences offering direct Atlantic Ocean views, a resort-style pool, pickleball court, and sandy beach with the flexibility of a weekly rental. The first floor offers a private two-car garage and covered cabana with spacious outdoor living space that leads out to the pool deck and beach. The second floor features an open floor plan with spacious kitchen, dining, and great room all overlooking the Atlantic Ocean. One en-suite bedroom on this floor provides seclusion for guests. On the top floor, you'll find the primary suite with a luxurious spa bath, a second guest suite and two additional guest bedrooms that share a bath. Luxuriously finished with high-end KitchenAid appliances, waterfall quartz countertops, full-height backsplashes, and much more. Additionally, this residence offers upgrades including an outdoor summer kitchen, an exterior spiral staircase from the second down to the first floor, and a fire pit. SeaGlass Cove is barefoot luxury at its best!

59720 Overseas Highway Unit 10, Marathon
$3,100,000
5 Beds ⋅ 5 Baths ⋅ 619896 MLS
CONSTRUCTION COMPLETE! MOVE-IN AND RENTAL READY! SeaGlass Cove is a brand-new luxury, gated island community located in the heart of the Florida Keys; adjacent to Duck Key. A rare find of just 14 new construction residences offering direct Atlantic Ocean views, a resort-style pool, pickleball court, and a sandy beach with the flexibility of a weekly rental. The first floor offers a private two-car garage and covered cabana with spacious outdoor living space that leads out to the pool deck and beach. The second floor features an open floor plan with spacious kitchen, dining, and great room all overlooking the Atlantic Ocean. One en-suite bedroom on this floor provides seclusion for guests. On the top floor, you'll find the primary suite with a luxurious spa bath, a second guest suite and two additional guest bedrooms that share a bath. Luxuriously finished with high-end KitchenAid appliances, waterfall quartz countertops, full-height backsplashes and much more. Additionally, this residence offers upgrades including an outdoor summer kitchen, an exterior spiral staircase from the second floor down to the first floor, and a fire pit. SeaGlass Cove is barefoot luxury at its best!

59720 Overseas Highway Unit 9, Marathon
$899,000
3 Beds ⋅ 3 Baths ⋅ 619891 MLS
Priced to sell! Welcome to your private slice of paradise in the heart of Key Largo! Designed for the buyer seeking relaxed and effortless island living, this beautiful home offers tons of space to play with: turn the second living room space into a bedroom and immediately get a 4/3 and make it's sundeck your favorite hangout area to watch the most stunning sunsets. You will love the indoor/outdoor feel with FOUR private balconies throughout the home for you to enjoy the coastal breeze and partial views of the bay. This home feels like a waterfront without the price tag! Inside, bright and open living spaces provide an inviting atmosphere for entertaining or unwinding after a day on the water. Outside, the low-maintenance yard allows you to spend less time on upkeep and more time enjoying the Florida Keys lifestyle, while still offering ample room and potential for a future pool to create your own private backyard retreat. Perfectly located a street away from Buttonwood Sound Club (Private homeowners club, membership required, $350 Annually), which offers a sandy beach and boat ramp and just one hour from Miami, this home is ideal as a full-time residence, vacation getaway, or investment property. Whether enjoying sunset views from your balcony or relaxing in the privacy of your tropical surroundings, this property embodies the easy elegance and laid-back luxury of the Upper Keys.

19 Park Dr, Key Largo
$679,000
5 Beds ⋅ 4 Baths ⋅ 619887 MLS
A versatile multi-unit opportunity in the heart of Tavernier. Offering three separate residences with a combined total of 5 bedrooms and 4 bathrooms, this property is well-suited for extended family living, income-producing potential, or a combination of both. Recent updates include a metal roof, updated kitchens with new appliances, new flooring in the front building, and a gas stove in the rear unit. The property also features a mix of impact windows, an impact sliding door, and shutters. Ideally located near Harry Harris Park, you'll have convenient access to a boat ramp, beach, oceanfront park, restrooms, and ball fields - where boating, beach days, and outdoor living are part of your everyday routine.

235 Antigua Rd, Tavernier
$7,500,000
5 Beds ⋅ 5 Baths ⋅ 619886 MLS
At the end of prestigious Sunrise Lane, where land meets open water on 3 sides, 3750 Sunrise Lane stands as one of the most extraordinary waterfront offerings in Key West. Properties of this scale and setting rarely exist, and almost never come to market. Originally built in the 1950s and extensively rebuilt in 1999, this legacy estate sits on a 28,500sf peninsula, offering a rare scale, privacy, and waterfront presence that is nearly impossible to replicate. The 5,378sf residence blends timeless architecture with expansive indoor and outdoor living. The main level features gracious living spaces with heart pine floors, French doors, and light-filled rooms opening to wide terraces and tranquil water views. The home offers 5 bedrooms and 4.5 baths, including 3 first-floor bedrooms and a spacious primary suite designed for comfort and privacy. Upstairs, 2 guest bedrooms open to a covered balcony and rare widow's walk with panoramic views of the Atlantic, Gulf, and surrounding protected lands. At the heart of the home is an expansive family-style kitchen with a large breakfast room, bar seating, desk area, and rich wood cabinetry. A handsome den with a built-in wet bar creates a warm gathering space, while a studio/flex room offers versatility as an office, art studio, fitness room, or guest overflow. The grounds are equally remarkable, featuring mature tropical landscaping, a large swimming pool, and over 3,200sf of brick patios. Nearly 500 linear feet of seawall provide exceptional dockage with a concrete dock and 2 boat lifts offering immediate deep-water access to both the Atlantic and Gulf. An oversized finished 828sf garage with 4 garage doors adds rare flexibility and functionality. This legacy estate awaits restoration and the vision of its next owner. Its setting, structure, and scale create a once-in-a-generation opportunity to reimagine one of Key West's most significant waterfront properties.

3750 Sunrise Ln, Key West
$1,750,000
3 Beds ⋅ 2 Baths ⋅ 619885 MLS
Welcome to Key Lime Kottage, a charming waterfront retreat in Grassy Key where life slows down, the water calls, and every day feels like a Florida Keys escape. Currently in a vacation rental program, this turn-key 3-bedroom, 2-bath home offers buyers and investors the rare combination of personal enjoyment, rental potential, privacy, and resort-style living. Kindly provide at least 24 hours' notice for showings. Preferred showing times are Saturdays during check-in/check-out windows, when access is most convenient. Tucked behind lush tropical landscaping, Key Lime Kottage welcomes you with soft yellow cottage charm, a metal roof, white picket appeal, and a peaceful waterfront setting that immediately invites you to relax. From the moment guests arrive, they can imagine themselves slowing down, breathing deeper, and enjoying the Keys lifestyle. A beautiful composite dock leads through the mangroves toward open Gulf views, creating the perfect place for morning coffee, kayaking, paddleboarding, sunset conversations, or quiet moments by the water. The outdoor living area is the heart of the property. With a screened-in pool, spa, covered lounging space, and natural privacy, it feels like a private resort designed for relaxation, connection, and unforgettable memories. Inside, the open living, dining, and kitchen layout feels warm, easy, and welcoming. The home is ready for immediate enjoyment, whether as a personal retreat, a vacation rental investment, or both. For investors, Key Lime Kottage offers strong guest appeal with waterfront living, Gulf views, pool and spa amenities, and proximity to the Dolphin Research Center, The Wreck Restaurant, downtown Marathon, grocery shopping, marinas, entertainment, and MillionAir. Buyers are not just purchasing a property here. They are stepping into peaceful mornings, golden sunsets, waterfront memories, and a Florida Keys lifestyle guests will want to return to again and again.

58773 Overseas Hwy, Marathon
$2,450,000
4 Beds ⋅ 5 Baths ⋅ 619881 MLS
Built in 2023 and already one of the busiest vacation rentals, this turnkey waterfront property delivers immediate income with 2026 bookings already in place. Designed from the ground up for serious boaters and guests who demand premium amenities. Every detail has been selected to drive occupancy, command top nightly rates, and minimize owner headaches. Located in popular Coco Plum, less than 10 minutes from the open water & Vaca Cut for Gulf access. 72' of deep water dockage, heated pool, paver decking, water & electric at dock with outdoor lighting, covered entertaining area, 240V EV charger, 800 sq ft storage enclosure, aluminum gate for secure vehicle access & security cameras for peace of mind. Follow the stairs up the back to the large covered terrace where you can find shelter in the shade while still enjoying the fresh salt air. Head through the double doors into the open kitchen and living area where you will find 4 master suites all with private bathrooms, tile flooring throughout, beautiful quartz countertops, tile backsplash, built in wine cooler and additional half bath. Property is being sold furnished from dishes to linens to smart tvs. Nothing to do but bring your boat and start enjoying the Keys Salt Life. Seller owns the bay bottom!

229 Pescayo Ave, Marathon
$2,269,800
3 Beds ⋅ 3 Baths ⋅ 619873 MLS
Welcome to your dream island retreat in Key Colony Beach! Featuring a BRAND NEW metal roof installed in May 2026, this exquisite above-flood, fully renovated Bill Ellison-built home offers 2,001 sq ft of upscale coastal living and peace of mind. Built in 1999 and ideally located on highly sought-after 12th Street, this boater's paradise provides quick and easy access to both the Gulf and Atlantic. Designed for entertaining and relaxation, the outdoor living space is exceptional. A spacious 15x15 tiki hut creates the perfect island gathering spot, while the expansive covered patio overlooks a stunning new 12x25 heated/chilled pool complete with a tranquil fountain feature. Boating enthusiasts will appreciate the 80 feet of deep-water concrete dockage, a 36-foot step-down wooden dock, and a convenient fish cleaning station. Inside, soaring 11-foot vaulted ceilings and luxury vinyl plank flooring create a bright, open atmosphere throughout. The beautifully renovated kitchen showcases elegant Dolomite countertops, under-counter island lighting, and brand-new stainless steel appliances. A spacious laundry room includes a new large-capacity washer and dryer for added convenience. Each of the three generously sized bedrooms features its own private ensuite bathroom. The primary suite is a true retreat, offering room for a sitting area, a large custom walk-in closet, and a luxurious ensuite bath featuring Carrera marble in the shower. Additional highlights include a 24x22 two-car garage, outdoor storage shed, dedicated boat trailer parking, and additional parking for two vehicles in front of the garage. For those seeking investment potential, Key Colony Beach allows 7-night vacation rentals, making this property an excellent opportunity for income-producing use. Plus, you're just a short stroll from Sunset Park where you can enjoy breathtaking Keys sunsets year-round.

641 12th St, Key Colony
$995,000
3 Beds ⋅ 2 Baths ⋅ 619877 MLS
This three bedroom , two bathroom home sits on an expansive 12,200 square foot piece of property in the highly sought after Breezeswept Beach Estates neighborhood on Ramrod Key. Upstairs there are two bedrooms and one bath, and a large kitchen and living room. Downstairs is a one bedroom, one bathroom bungalow with a complete kitchen! The exterior of the property has several updates, including storage sheds, 90 feet of brand new docks with water, electric and a brand new built in fish cleaning table. A new roof was installed in 2023. Plenty of room to stretch out on this property, lots of parking, room for boat trailers, and totally fenced in for your pets. Excellent location for open water access, short canal ride and a couple minutes to picnic island for a relaxing afternoon and sunset!

750 W Indies Dr, Ramrod
$950,000
3 Beds ⋅ 2 Baths ⋅ 619875 MLS
On a quiet dead-end street in the highly sought-after Sugarloaf Shores community, sits this fully renovated tropical retreat thats reminiscent of something straight out of a secret garden. Set on an oversized, gated and partially fenced parcel spanning over a quarter acre, this rare non-waterfront property offers the kind of lush green space that's nearly impossible to find in the Florida Keys. Towering old-growth foliage, vibrant established plantings, fresh new landscaping, and newly laid sod create a private, enchanted oasis where every corner invites you to slow down and stay awhile. Built in 1981 of solid concrete block construction and elevated on slab, this beautifully reimagined 3-bedroom, 2-bathroom home offers 1,548 square feet of airy, light-filled living space with bright neutral finishes and thoughtful details throughout. Every inch has been meticulously renovated, blending modern comfort with effortless island charm. Designed to embrace indoor-outdoor living, the property features multiple lanais and entertaining spaces perfect for morning coffee beneath the palms, sunset dinners with friends, or quiet afternoons surrounded by tropical serenity. The expansive lot offers endless opportunity for future enhancements -- envision a resort-style pool and tiki hut, a greenhouse, outdoor kitchen, play space for the kids, or all of the above. There's room here to truly create your dream Keys compound. Downstairs, nearly 400 additional square feet of enclosed storage and utility space adds incredible flexibility, while the paved 3-car carport with lighting and built-in workspace could easily be transformed into the ultimate outdoor entertaining kitchen or hobby space. Beloved Sugarloaf Shores provides peaceful island living with a scenic miles-long paved path, a laid-back Lower Keys atmosphere, and sought-after school district -- all just 15 minutes from exciting Key West. Rare Keys privacy, greenery, and possibility you may never want to leave.

123 Venetian Way, Sugarloaf
$3,199,000
3 Beds ⋅ 2 Baths ⋅ 619869 MLS
Beautifully renovated oceanfront home in Islamorada offering 100 feet of direct ocean frontage, a sandy beach, breathtaking open water views, and mature tropical landscaping. This exceptional concrete stilt home has undergone a spectacular extensive coastal renovation, blending modern luxury with the relaxed elegance of the Florida Keys lifestyle. The residence features 3 bedrooms and 3 bathrooms with a bright, open-concept floor plan designed to maximize natural light and panoramic ocean views. The upstairs living quarters include a stunning new chef's kitchen with custom cabinetry, premium countertops, and high-end appliances, along with beautifully renovated bathrooms and spacious living and dining areas that flow seamlessly onto the elevated oceanfront porch. Recent upgrades include a brand new roof, all new impact windows and doors, renovated bathrooms, a fully redesigned kitchen, updated finishes throughout, and extensive coastal improvements designed for both style and durability. The gated and fenced property also features a gorgeous oceanfront swimming pool with updated pool equipment, outdoor shower, covered parking for multiple vehicles and boats, and abundant storage space. Outdoor enthusiasts will appreciate the impressive 90-foot oceanfront fishing pier with concrete pilings and low-maintenance composite decking, creating the perfect setting to fish, relax, entertain, or take in the spectacular sunrise views over the Atlantic Ocean. This is a rare opportunity to own a fully renovated luxury oceanfront retreat in Islamorada, known as the ''Fishing Capital of the World.''

75071 Overseas Hwy, Islamorada
$1,250,000
2 Beds ⋅ 2 Baths ⋅ 619868 MLS
Location, location, location. This home has stunning sunrise and ocean views from this one- of-a kind Open Water property. Picture perfect views from theFrench Doors off of the living room leading onto a sprawling deck overlooking the turquoise water. This home has a pool and is a spacious 2 Bedroom 1.5 Bath with a loft. Dock with 7,000lb. boat lift and storage enclosure.

257 La Fitte Rd, Little Torch
$1,399,000
2 Beds ⋅ 2 Baths ⋅ 619865 MLS
Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a private island atmosphere while the standing seam galvanized roof and concrete construction provide lasting durability and peace of mind. Inside, the home radiates warmth and coastal character. Vaulted wood tongue-and-groove ceilings draw your eyes upward and create an airy, open feel throughout the living spaces. The thoughtfully designed floor plan flows seamlessly between the kitchen, dining, and living areas, making the home ideal for entertaining family and friends after a day on the water. The kitchen is both stylish and functional with updated stainless appliances, generous cabinetry, pantry and a large dining bar for casual dining. Picturesque pool and water views are enjoyed from the living areas and primary suite. Outside is where this property truly shines. The new waterfront pool creates a resort-style centerpiece from the living area and is surrounded by multiple lounging and entertaining spaces. Relax beneath the tiki hut with a morning coffee, gather around the waterfront firepit at sunset, or enjoy evenings under the stars with the gentle breeze coming off the canal. For boating enthusiasts the deep-draft canal accommodates larger boats with a new 17K boat lift and quick ocean access. The nearby full-service marina offers fuel, bait, refreshments and boat ramp access while the neighborhood waterfront restaurant adds another layer of convenience and charm. Plenty of room for of your gear and toys in the 2-car attached garage. Located 20 minutes from Key West offering the perfect balance between peaceful island living and access to world-class dining and culture.

21012 6th Ave, Cudjoe
$1,199,000
3 Beds ⋅ 3 Baths ⋅ 619848 MLS
Experience all that Islamorada has to offer from this stunning home that was constructed in 2020. This two-story residence offers 3 spacious bedrooms and 2 full bathrooms on the ground floor. The second floor has a large great room - ideal for a home office, second living room, playroom, or media space--adding extra versatility to the layout. Additionally, there is another full bathroom upstairs. Step into an open-concept main living area with numerous windows to let in the natural light. Easy to clean tile throughout. The heart of the home is a modern kitchen featuring a large island, custom cabinetry, and premium finishes--perfect for entertaining and everyday living. The spacious side and backyard provide ample space for trailers, boats, or a future pool, making it perfect for outdoor enthusiasts. Speaking of pool, there is a current, valid pool permit that has been issued for the property and can be transferred to the next owner. This home is located just minutes from the ocean, marinas, shopping, and dining. It is zoned for highly rated Coral Shores High School. This home offers the rare opportunity to own an almost new, move-in-ready property in the Upper Keys. Don't wait--schedule your private showing today and make this modern island retreat your forever home!

143 N Hammock Rd, Islamorada
$3,750,000
4 Beds ⋅ 4 Baths ⋅ 619842 MLS
Morning Glory - The Dolphin House is one of those rare oceanfront sanctuaries where time softens, stress fades, and every sunrise feels like it was created just for you. Welcome to Morning Glory - The Dolphin House. There are homes you visit... and there are homes you feel the moment you arrive. Perfectly positioned on an oversized direct oceanfront lot, this extraordinary 4-bedroom, 3.5-bathroom residence with 2,478 square feet invites you into a lifestyle many dream about--but few ever experience. As you step inside, you are greeted by tasteful coastal elegance, natural light, and sweeping blue-water views that instantly quiet the mind. Every room feels intentional, warm, and beautifully curated. The décor blends sophistication with comfort, creating a space where luxury feels effortless. Imagine waking each morning in your private suite as the first golden light rises over the Atlantic. Open your eyes to endless turquoise water, soft breezes, and the promise of another perfect day. Walk onto the expansive veranda with your morning coffee, where the sunrise slowly paints the sky. In the evening, the moonrise becomes your private show--silver light dancing across the water while the world grows still. Outside, the experience becomes unforgettable. Spend afternoons floating in the pool beneath swaying palms. Gather friends and family for waterfront dining as laughter mixes with the ocean breeze. Slip into the hammock with soft music and your favorite book. End the night beside the fire pit with a warm drink, toasted marshmallows, and stories under a sky full of stars. This is more than a beautiful home. It is where memories are created. Where families reconnect. Where success is celebrated. Where peace returns. For the buyer who has worked hard and now wants to truly live well, Morning Glory - The Dolphin House is not just a property. This is more than a beautiful oceanfront home. It is where memories are created. Where families reconnect. Where success is celebrated. Where peace returns. For the buyer who has worked hard and is ready to live well, truly, Morning Glory - The Dolphin House is not just a property. It is a reward. It is a retreat. It is a lifestyle. It is your chance to own a piece of oceanfront paradise.

17387 E Dolphin St, Sugarloaf
$869,000
2 Beds ⋅ 2 Baths ⋅ 619841 MLS
Seller Welcomes Offers! Tucked away on a quiet dead-end street in Big Pine Key, this beautifully updated 2-bedroom, 2-bath canal-front home offers the perfect blend of modern comfort and relaxed island living. Thoughtfully renovated throughout, the home features updated flooring, stylishly remodeled bathrooms, a sleek contemporary kitchen, fresh exterior paint, and upgraded decking and screening, creating a truly turnkey island retreat. The spacious screened porch extends the living area outdoors, providing an inviting setting to relax, entertain, and enjoy the gentle island breezes year-round. Outside, unwind along the canal and take advantage of the durable composite dock with quick boating access to Pine Channel--perfect for fishing excursions, waterfront dining by boat, or unforgettable sunset cruises. Whether you're searching for a full-time residence, seasonal escape, or weekend getaway, this exceptional property captures the charm, tranquility, and effortless lifestyle that make the Florida Keys so desirable.

3674 S Seas St, Big Pine
$1,198,000
3 Beds ⋅ 3 Baths ⋅ 619838 MLS
Winston Waterway canal front house. Large corner lot with enough room for 2 davits ; metal roof; 3 bed 2.5 bath and a loft with wet bar with a den.

100 3rd Ln, Key Largo
$2,150,000
5 Beds ⋅ 3 Baths ⋅ 619837 MLS
A rare opportunity to own a fully renovated waterfront home that delivers both the Florida Keys lifestyle and exceptional investment potential. Offering five legal bedrooms, three legal bathrooms, and seven-day vacation rentals, this turnkey property presents projected rental income of up to $170,000 annually (per pro forma), making it equally appealing as a primary residence, second home, or income-producing investment. Located on a deep-water canal with approximately 75 feet of concrete dockage, a boat lift, fish-cleaning station, and private pool, you'll enjoy quick, easy access to the Gulf and the Atlantic through Vaca Cut--putting world-class fishing, sandbars, waterfront restaurants, and open water just minutes from your dock. Inside, the home has been completely reimagined with designer finishes throughout. An open-concept floor plan, beautifully renovated kitchen and baths, and light-filled living spaces create a sophisticated yet relaxed coastal retreat that's ready to enjoy from day one. With generous parking for vehicles and trailers, ample outdoor entertaining space, and one of Marathon's most desirable boating locations, this property offers a rare combination of luxury, convenience, and strong income potential. Whether you're looking for a high-performing vacation rental or your own private piece of the Florida Keys, this home delivers the best of both.

112 Bruce Ct, Marathon
$450,000
2 Beds ⋅ 2 Baths ⋅ 619836 MLS
Affordable Living in the Florida Keys Has Arrived! Welcome to this charming 2-bedroom, 2-bathroom home offering comfortable living space, an open-concept layout, and inviting outdoor areas perfect for dining, entertaining, or simply enjoying our beautiful Florida Keys lifestyle. Step inside to a bright and open living room and kitchen just off the front entry. Both bedrooms are privately situated toward the back of the home. The Primary bedroom includes direct access to the backyard area, an ensuite bathroom with walk-in shower, and plenty of closet/storage space. Qualified buyers may have the opportunity to assume the current mortgage, VA and FHA buyers this home is a must see. Additional highlights include ample parking, a great neighborhood, and a convenient location just minutes from Bay View Park, Baby's Coffee, the famous Sugar Shark Market, and NAS Key West on Boca Chica. Come see this home now, at this price, this one will not last long!!

4 Coral Dr, Saddle Bunch
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 619835 MLS
Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete block residence offers 1,434 square feet of refined coastal living, enhanced by rich wooden ceilings that add warmth, character, and timeless island charm. The open living spaces flow effortlessly to the screened porch overlooking the canal -- the ideal setting for morning coffee, sunset cocktails, or unwinding after a day on the water. Designed with both comfort and functionality in mind, the property features a new metal roof, covered parking, fenced grounds, and a spacious downstairs utility/workshop area perfect for boating gear, paddleboards, fishing equipment, or hobbies. Perfectly positioned on a canal in the Lower Keys with easy boating access, Rooftop Retreat captures the essence of waterfront living with unforgettable ocean vistas and an inviting coastal atmosphere. Whether you're searching for a private island getaway, a second home, or an exceptional investment opportunity, this property delivers the very best of the Keys lifestyle.

22939 Gasparilla Ln, Cudjoe
$40,000,000
8 Beds ⋅ 11 Baths ⋅ 619826 MLS
A rare dual-offering on coveted Millionaire's Row in Tavernier, this extraordinary oceanfront compound spans over multiple acres across two parcels-delivering an unmatched combination of scale, privacy, and future development flexibility in the Florida Keys. At 88845, a newly constructed 8,200SF estate sets a new standard for modern coastal luxury. Thoughtfully designed for both grand entertaining and private retreat, the residence offers 5 bedrooms, 6 full baths & 2 half baths, complemented by a dedicated office, control room, mudroom, and expansive 3-car garage with climate-controlled workshop. Interior finishes are curated at the highest level, including white diamond marble, teak wood flooring, custom millwork & a vapor fireplace, while a full-home sound system, elevator & advanced mechanical infrastructure provide seamless functionality. The chef's kitchen is equipped with top-tier Wolf, SubZero, & Cove appliances, dual dishwashers, farmhouse sinks, refrigerated drawers, wine storage & custom mahogany countertops-designed to accommodate both everyday living and large-scale entertaining. Outdoor living is equally impressive, anchored by a 120-foot resort-style pool with integrated spa, heating & chilling systems, & full smart control. A fully equipped summer kitchen, cabana bath, & multiple covered terraces create a true waterfront lifestyle experience. With 480 feet of water frontage, the protected basin offers exceptional boating capabilities, including 90 feet of dockage & room to expand, a 20,000lb lift, boat ramp & deep-water access. The adjacent parcel at 88835 provides over 3 acres of additional opportunity featuring a renovated 3-bedroom residence completed in 2022, with a transferable TDR allowing for the development of a substantially larger primary home. The property also includes a buildable lot & natural hammock buffer for added privacy. Together, these two properties present a generational opportunity to own a one of a kind waterfront compound.

88835 & 88845 Old Hwy, Tavernier
$27,000,000
5 Beds ⋅ 8 Baths ⋅ 619825 MLS
Set on over 2 acres along prestigious Millionaire's Row in Tavernier, this newly constructed oceanfront estate represents a rare convergence of scale, design, and functionality in the Upper Florida Keys. Encompassing 8,200 square feet of interior living space and over 16,000 square feet total, the residence is thoughtfully designed to accommodate both elevated everyday living and large-scale entertaining.The home features 5 bedrooms, 6 full baths, and 2 half baths, with all bedrooms offering en suite accommodations, custom closet build-outs, and refined finishes throughout. Additional interior spaces include a dedicated office, control room, mud room, and laundry room, providing both comfort and operational efficiency. A private elevator, whole-home sound system, and advanced mechanical infrastructure--including 600-amp service, multiple electrical panels, and five independent AC zones--underscore the property's level of detail and performance. Interior finishes are curated with a modern coastal aesthetic, highlighted by white diamond marble and teak wood flooring & a custom steel roof. The chef's kitchen is outfitted with top-tier Wolf, SubZero, and Cove appliances, including a 60-inch range, dual dishwashers, farmhouse sinks, and custom mahogany countertops--designed to seamlessly blend form and function. Outdoor living is equally exceptional, with 240 feet of oceanfront, anchored by a 120-foot resort-style pool, complete with multiple heating and chilling systems, a gas-heated spa, and full smart control. A fully equipped summer kitchen, cabana bath, and multiple covered entertaining areas create a true indoor-outdoor lifestyle experience. Additional highlights include a 3-car garage and fully equipped workshop with air conditioning, utilities, security systems, and custom lighting. The property is also zoned for weekly rentals, presenting a compelling opportunity for both personal enjoyment and income potential.

88845 Old Hwy, Tavernier
$15,000,000
3 Beds ⋅ 3 Baths ⋅ 619824 MLS
An exceptional opportunity on coveted Millionaire's Row in Tavernier, 88835 Old Highway offers over 3 acres of oceanfront property paired with a rare additional acre featuring a protected boat basin--delivering a unique blend of privacy, usability, and future potential in the Upper Keys. Completed in 2022, the existing 3-bedroom, 3 bath residence spans approximately 1,500 square feet and is thoughtfully designed with impact windows and doors, hardwood flooring, a steel metal roof, and a well-appointed kitchen featuring Viking appliances. Outdoor living is enhanced by shell stone porch flooring, covered parking, and professionally designed landscaping with turf for low-maintenance coastal living. The property is comprised of three distinct parcels, including a buildable lot (Lot 2A), the current homesite (Lot 2), and a natural hammock parcel (Lot 3A) that serves as a permanent privacy buffer from the road, preserving the integrity and seclusion of the estate. A highly valuable feature of this offering is the inclusion & rare opportunity to create a custom waterfront compound tailored to your vision, while maintaining immediate livability. With direct access to a private boat basin and expansive acreage rarely found in the Keys, 88835 Old Highway represents a compelling combination of current enjoyment, future development flexibility, and long-term value in one of the area's most desirable waterfront corridors.

88835 Old Hwy, Tavernier
$1,055,000
3 Beds ⋅ 2 Baths ⋅ 619820 MLS
Accessibility elevator! Welcome to your Lower Keys retreat where comfort, and coastal living come together beautifully along with the convenience of an interior elevator. Situated on the desirable boating canal system of Pine Channel Estates, this 3 bedroom, 2 bath home is designed for those who appreciate the water based lifestyle. Inside, soaring vaulted ceilings create an open and airy atmosphere throughout the home, while the interior elevator offers effortless and/or handicap access and convenience. Expansive living spaces flow seamlessly onto a large screened deck and two additional open-air decks off of the canal side bedrooms, all perfectly positioned to capture peaceful canal views. Elevated above flood and built to withstand severe weather conditions with impact resistant windows and metal roof. For boating enthusiasts, this property is truly exceptional. Featuring two boat docks and a 12,000-pound boat lift, you'll enjoy quick and easy access to the ocean and gulf side right from your backyard. Whether you're heading out for a day on the boat, entertaining guests outdoors, or simply relaxing in the coastal breeze, this home delivers the ultimate waterfront lifestyle. **Handicap accessible with interior elevator shaft ~ Sewer assessment is paid in full ~ Fire & Liability (homeowners) insurance $2,318.30**

29555 Enterprise Ave, Big Pine
$13,000,000
5 Beds ⋅ 5 Baths ⋅ 619817 MLS
Discover Turtle Crawl, the ultimate private sanctuary on the shimmering shores of Long Key -- a rare gated oceanfront estate encompassing nearly one acre of pristine tropical beauty and a powdery white-sand beach. This exclusive 5-bedroom, 5-bath residence invites you to embrace a lifestyle defined by serenity, wellness, and effortless connection to the sea. Spanning over 5,000 square feet of elevated concrete construction, the home captures breathtaking panoramic Atlantic views from nearly every room. Soaring cathedral ceilings and an open-concept design create a sense of boundless space, bathed in natural light. Four spacious bedrooms on the main level offer refined comfort, while the second-floor entertainment lounge and widow's walk reveal mesmerizing vistas of both the Ocean and Gulf -- a true testament to the beauty of the Keys. Outdoors, your private resort oasis awaits. A 40-foot resort-style pool glistens amidst swaying palms, framed by an expansive covered veranda perfect for alfresco dining, yoga at sunrise, or sunset cocktails by the sea. Begin your morning with gentle stretches on the sand as the ocean breeze flows around you, or indulge in a private seaside massage beneath the palms for the ultimate relaxation. The soft, white-sand beach invites laughter and family fun -- building sandcastles, paddleboarding together, or exploring the turquoise waters from your private dock with a 16,000 lb lift and 4-ft draft. Perfectly positioned between Islamorada and Marathon, this Long Key jewel offers the rare combination of tranquility and convenience. Whether hosting a sunset soirée, sharing quality time with loved ones, or escaping into a moment of stillness by the sea, Turtle Crawl embodies the ultimate Florida Keys lifestyle -- luxurious, rejuvenating, and deeply connected to nature. Experience the essence of oceanfront living in the heart of the Florida Keys. Call to arrange your private showing!

65760 Overseas Hwy, Layton
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 619797 MLS
This extraordinary Mid-Century modern single-family home is a private tropical oasis at the (rarely available) end of a canal with direct-ocean access. The luxury resort-style patio features Travertine tile, a heated pool with a sun shelf, and custom landscape lighting for evening entertaining. The home's original craftsmanship is high-lighted by tongue and groove Florida Pine ceilings, grand archways, and wooden beams. The floor to ceiling windows and doors provide for natural light flowing into the home from sunrise until sunset. The open-concept living area connects to an updated kitchen with stainless steel appliances and granite countertops. The master suite boasts a hand-scraped Acacia Hardwood accent wall, barn doors, an oversized Travertine shower, and a floating sink. Two additional bedrooms in a separate wing provide guest privacy with a shared updated bathroom with an Italian marble shower. This oversized fenced lot at 8,362 sq/ft provides a tropical sanctuary in paradise. Whether you're looking for an established and profitable rental property or you're ready to embrace the dream of a Florida Keys lifestyle, this turnkey property delivers.

280 100th St, Marathon
$999,000
4 Beds ⋅ 3 Baths ⋅ 619796 MLS
Spacious 4 bed, 3 bath home in the desirable Indian Mound neighborhood on Plantation Key. Sitting on two lots totaling about 11,000 sq ft, there's plenty of privacy and extra space to enjoy. As you enter, you're welcomed by a large, open floor plan with high ceilings, giving the home a bright and airy feel. The kitchen features granite countertops, upgraded stainless steel appliances, and high-output tankless water heater with instant hot water. Tile flooring runs throughout the main level, with carpet upstairs. Just off the living room, there's a large screened-in outdoor space that's perfect for relaxing or entertaining. This ground-level, above-flood CBS home was built in 2010 and includes a metal roof, impact windows and doors, split-zone A/C, and ceiling fans throughout. It offers 2,361 sq ft of living space, along with exterior lighting and a fenced backyard. Located at 148 Iroquois St and close to local schools, it's a great option for anyone needing both space and convenience. The oversized lot gives you room for kids, pets, or even future additions, while the fenced yard adds an extra layer of privacy. The neighborhood also offers a boat ramp, making it easy to enjoy everything the Keys lifestyle has to offer.

148 Iroquois St, Tavernier
$599,000
2 Beds ⋅ 1 Baths ⋅ 619795 MLS
Charming Key Largo Retreat Near the Water... Taking in the Bay Breeze. Just under an hour from Miami, discover this picture-perfect 'dollhouse' nestled on sought-after Ocean View Blvd. Surrounded by magnificent waterfront estates and located just moments from world-famous Snappers, this home offers the perfect blend of charm, location, lifestyle, and investment potential. Situated on a 5,780 SF lot, Zone Flood X this impeccably maintained home features beautiful terrazzo floors, newer A/C, newer washer and dryer, newer refrigerator, and hurricane-impact windows and doors, providing comfort and peace of mind. The spacious yard offers room for a boat, RV, or future expansion, with covered parking already in place. Whether you envision adding a pool, expanding the home, or enjoying it exactly as it is, the possibilities are endless. Previously enjoyed as a seasonal residence, the property may also appeal to buyers exploring vacation rental opportunities. Its classic Florida Keys cottage style, manageable size, and proximity to boating, diving, fishing, dining, and local attractions make it well suited for seasonal visitors. Buyers are encouraged to independently verify vacation rental regulations, licensing requirements, and projected rental income during their due diligence. Whether you're seeking a full-time residence, weekend escape, or potential income-producing investment, this Key Largo gem is ready to welcome its next owner. Your slice of the Keys lifestyle awaits! Owner financing may be considered for qualified purchasers acquiring the property as a non-homestead/non-owner-occupied residence with a minimum $400,000 down payment. Illustrative terms include a loan at 9% interest, amortized over 30 years with a 5-year balloon, with principal and interest payments only. All owner financing terms are subject to seller approval.

8 Ocean View Blvd, Key Largo
$2,249,000
4 Beds ⋅ 3 Baths ⋅ 619793 MLS
Over 3400 sqft of Luxury Living is featured with this 2007 custom built CBS in the gated community of Stirrup Key Sub in Marathon. Elevated water views, a deeded boat slip, protected community marina, multiple outdoor living areas and a private pool. Designed for both everyday comfort and entertaining, this multi-level home offers generous interior space, flexible living areas, and a thoughtful indoor-outdoor layout. The ground level features a three-car garage, ample storage, and direct access to the pool area, creating an easy flow for relaxing, hosting, and enjoying the Keys lifestyle. The second floor serves as the main living level with two bedrooms, two full baths, a full kitchen, and open living and dining areas that extend onto a large screened lanai. This level is ideal for casual gatherings, quiet mornings, and evening breezes. The third floor offers a private primary suite, sitting area or fourth bedroom, bar/kitchenette, fireplace, spa-style bath, and an expansive lanai with peaceful elevated views. A spiral staircase leads to the fourth-floor widow's walk, finished with travertine flooring and a water hookup. From this vantage point, panoramic views stretch across Marathon and toward the Gulf, creating a quiet setting for sunrise, sunset, and open-air relaxation. A private nature path winds through preserved surroundings and leads to a Gulf-front observation dock, ideal for wildlife viewing and enjoying the surrounding natural setting. Additional features include a lift to the second floor for added convenience. Centrally located in Marathon, the home offers convenient access to shopping, dining, & daily necessities. With a deeded marina slip, elevated water views, pool, garage space, storage, multiple lanais, and a flexible custom layout, this property offers a rare combination of privacy, space, and boating access in Marathon. Schedule a private showing to experience this custom home and deeded marina slip in person.

205 Stirrup, Marathon